Allessan® CAP

An outstanding coupling and water-removal reagent

Allessan®CAP is an outstanding coupling and water removal reagent, offering numerous advantages over many other commonly used but hazardous coupling reagents such as DCC (toxic), HOBt (explosive), HBTU, and PyBOP.

Thanks to its less toxic properties, a broad spectrum of applications, high selectivity, and mild operating conditions, Propanephosphonic Acid Anhydride (PPAA) (also known as PPA-Polyphosphoric acid or T3P) offers you several benefits in both medicinal chemistry and chemical processes, including:

High chemical and optical purity
High product purities
Excellent yields
Reduced overall process costs

Benefits
Applications
Benefits of PPA vs common coupling reagents
Comparison of the degree of racemization of different coupling reagents
Facility
Technical specification
Chemical Formula

Safe handling – no CMR properties, non-toxic, non-allergenic, non-sensitizing
Excellent safety profile: high thermal stability, no decomposition
Broad functional group tolerance, mild reaction conditions (0 –25 °C)
Well established at large-scale for challenging liquid phase amide/peptide coupling reactions
Low epimerization, no additives required
Excellent selectivity, high chemical and optical purity, high product purities, and excellent yields
Easy purification/workup due to water-soluble by-products, no need of further purifications
Simple product isolation by liquid/liquid extraction and phase separation
Reduced overall process costs
Long shelf life (> 36 months)
No special storage required

Allessan®CAP can be used for:

Amidations and Peptide couplings in the liquid phase (linear and cyclic peptides)
Esterifications
Functional Group Transformation (nitrile formation, olefine formation, alcohol oxidation, reduction of carboxylic acids, Lossen rearrangement, Beckmann rearrangement)
Synthesis of heterocyclic compounds (pyrazolone, indole, quinolines, coumarins)
Swern-type oxidations as a substitute of oxalyl dichloride and triethylamine
Aza-Diels-Alder reactions as a catalyst
pH neutral dehydration reagent, similar in strength to the highly reactive and hazardous phosphorous pentoxide and polyphosphoric acid
Alternative to molecular sieves for water removal from organic solvents
Lewis acid catalysis

Coupling Reagent	Toxicity	Epimirization	Yield	Purification	Costs
PPA	No	Low	High	Simple	Medium
DCC	High	High	Low	Very difficult	Low
DCC/HOBt	High	Medium	Medium	Very difficult	Low
EDC	High	Medium	Medium	Simple	Medium
BOP	Very high	Low	High	Difficult	High
PyClop	Medium	Low	High	Difficult	Very high
TBTU/HBTU	Medium	Low	High	Difficult	Medium

Coupling Reagent	Racemization (%)	Yield (%)
PPA	1.8	86.6
HOBt/DCC	5.9	60.5
HOBt/EDC	11.1	67.3
HOAt/DCC	11.6	N/A
PyBOP	14.2	63.4
HBTU	16.1	65.6
HATU	21.1	N/A

Facility

Produced in an ISO 9001 certified facility
Capacity: several hundred tons per year

Variety of Solvents

Allessan®CAP is typically offered as a concentrated 50% (w/w) solution in various kinds of solvents.

Ethyl acetate and THF are the most widely used, however, Allessan®CAP can be available in many other solvents (DMF, 2-Me-THF, Acetonitrile, Dichloromethane, Toluene)

Packaging

5 L, 50 L, 200 L steel drums with PE inliners or twin-lock drums (DMF)
Only 5 L drums are allowed to be shipped by air freight

	ALLESSAN®CAP
Name	PPAA (Propanephosphonic acid anhydride), also shortened to PPA (Polyphosphoric acid) or T3P
Empirical formula	[C3 H7 O2 P]3
Molecular weight (g/mol)	318.18
CAS No.	68957-94-8
Appearance	Clear solution
Active content (%w/w)	Min. 50
Solvent content (%w/w)	40 – 44.5
Content of solvent-free Allessan®CAP* (%w/w)	55.5 – 60
Hydrogen chloride content of Allessan®CAP solution (%)	< 0.1

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